Using Outlook for Mac; emails and calendar announcements will not send--error message: "the server does not support secure connections" Help?

Am using Outlook calendar for Mac--needed for client connection. Invites will not go out. Error message: "server does not support secure connections." Resolution?

I have done a similar set of things and no results.
This is really odd, Mac Mail works other emasil clients work, just not Outlook.
The only event I can tie it back to is the outage a couple of weeks ago when AppleID's weren't working for a perdion of time.  I ended up having to reset mine. 
Is it feasible a local certificate got corrupted at the same or, oddly, that the SMTP servers don't have the updated password?
What's odd is that I no matter how much i Google, i can't find anyone else who has this problem, other than here?

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